Around Boston | 3 Days & 2 Nights in Maine’s Small Towns

I’ve leveled up—I took my kid on a road trip to Maine for the second time! I’ve always thought Boston is like the “Ningguta of North America” (a lighthearted reference to it feeling less exciting) and a total “food desert.” But surprisingly, it’s not that bad when compared to Maine! 📝 Day 1 📍 Seashore Trolley Museum: Our hotel didn’t allow check-in until 3 PM, so I found this trolley museum on Google Maps. My kid has been obsessed with all kinds of vehicles lately, so it was the perfect detour. We left around noon on Saturday to avoid traffic, and the drive was super smooth—we arrived in an hour and a half. Besides the museum’s own trolleys, there’s also a national chain railbike experience here. A 4-person railbike costs just over $100, and the price even includes admission to the museum 🚂! We learned about the rise and fall of trolleys, trolley parks, and eventually trolley museums. We also got to see a retired Boston Green Line Line A trolley—super interesting! Maybe our driving was too smooth because my kid slept through most of the trip 😴. 📝 Day 2 📍 Maine Cliff House: We caught the sunrise on the hotel’s big terrace in the morning—the view was so wide and unobstructed 🌅! 📍 Ogunquit Beach: Check the tide schedule before you go—try to arrive half an hour before low tide so you can play longer. When we got to the parking lot at 9 AM, it was already almost full, and parking costs $5 per hour 🅿️. This summer was so short; by early September, the seawater was already a bit cold. It was my kid’s first time digging in the sand and stepping in the sea—they played all morning and refused to leave 🏖️! 📍 Ogunquit Museum of American Art: It’s a small art museum with very limited parking. It’s located right by the sea, so the scenery is nice, but admission is $15. It’s one of those “we’re already here, so why not” spots 🎨. The highlight of its collection is a portrait of Hemingway—definitely optional, not a must-visit. 📝 Day 3 📍 Perkins Cove: The parking lot isn’t big, but since there are attractions nearby, you need to arrive early. When we got there around 9 AM, only a few spots were left. The landmark here is the Footbridge, which opens up in the middle, and the bay is filled with yachts ⛵️. The streets are lined with small shops selling “Yiwu-style” crafts—even a tiny dipping plate costs $40, which was way too pricey for me to buy 🛍️. 📍 Marginal Way: It’s right next to Perkins Cove—a 1.25-mile coastal trail that’s perfect for strolling with kids 🚶. #AroundBoston #Maine #Railbike #MaineTravel #Ogunquit #York #Kennebunkport